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Silver-catalyzed three-component reaction: synthesis of N2-substituted 1,2,3-triazoles via direct benzylic amination

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Abstract

A novel Ag(I)-catalyzed benzylic amination reaction with in situ generation of NH-1,2,3-triazoles for N2-substituted 1,2,3-triazole scaffolds is described. This protocol is achieved with easily accessible substrate, broad functional group, good regioselectivity, thus providing the efficient and practical method to diverse N2-substituted 1,2,3-triazole rings with moderate to good yields.

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References

  1. Davies HML, Alford JS. Chem Soc Rev, 2014, 43: 5151–5162

    Article  CAS  PubMed  Google Scholar 

  2. Huang D, Zhao P, Astruc D. Coordin Chem Rev, 2014, 272: 145–165

    Article  CAS  Google Scholar 

  3. Hosseyni S, Wojtas L, Li M, Shi X. J Am Chem Soc, 2016, 138: 3994–3997

    Article  CAS  PubMed  Google Scholar 

  4. Ye X, Xu C, Wojtas L, Akhmedov NG, Chen H, Shi X. Org Lett, 2016, 18: 2970–2973

    Article  CAS  PubMed  Google Scholar 

  5. Goitia A, Gómez-Bengoa E, Correa A. Org Lett, 2017, 19: 962–965

    Article  CAS  PubMed  Google Scholar 

  6. Kacprzak K, Skiera I, Piasecka M, Paryzek Z. Chem Rev, 2016, 116: 5689–5743

    Article  CAS  PubMed  Google Scholar 

  7. Kolb HC, Sharpless KB. Drug Discovery Today, 2003, 8: 1128–1137

    Article  CAS  Google Scholar 

  8. Whiting M, Tripp JC, Lin YC, Lindstrom W, Olson AJ, Elder JH, Sharpless KB, Fokin VV. J Med Chem, 2006, 49: 7697–7710

    Article  CAS  PubMed  Google Scholar 

  9. Wilkinson BL, Bornaghi LF, Houston TA, Poulsen SA. In: Kaplan S P, ed. Drug Design Research Perspectives. Nova: Haupauge, 2007. 57

    Google Scholar 

  10. Chrovian CC, Soyode-Johnson A, Peterson AA, Gelin CF, Deng X, Dvorak CA, Carruthers NI, Lord B, Fraser I, Aluisio L, Coe KJ, Scott B, Koudriakova T, Schoetens F, Sepassi K, Gallacher DJ, Bhattacharya A, Letavic MA. J Med Chem, 2018, 61: 207–223

    Article  CAS  PubMed  Google Scholar 

  11. Zheng Y, Ji X, Yu B, Ji K, Gallo D, Csizmadia E, Zhu M, Choudhury MR, De La Cruz LKC, Chittavong V, Pan Z, Yuan Z, Otterbein LE, Wang B. Nat Chem, 2018, 10: 787–794

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Tiwari VK, Mishra BB, Mishra KB, Mishra N, Singh AS, Chen X. Chem Rev, 2016, 116: 3086–3240

    Article  CAS  PubMed  Google Scholar 

  13. Kim WG, Choi B, Yang HJ, Han JA, Jung H, Cho HJ, Kang S, Hong SY. Bioconjugate Chem, 2016, 27: 2007–2013

    Article  CAS  Google Scholar 

  14. Thirumurugan P, Matosiuk D, Jozwiak K. Chem Rev, 2013, 113: 4905–4979

    Article  CAS  PubMed  Google Scholar 

  15. Tang W, Becker ML. Chem Soc Rev, 2014, 43: 7013–7039

    Article  CAS  PubMed  Google Scholar 

  16. Tian H, Fürstenberg A, Huber T. Chem Rev, 2017, 117: 186–245

    Article  CAS  PubMed  Google Scholar 

  17. Finn MG, Fokin VV. Chem Soc Rev, 2010, 39: 1231

    Article  CAS  PubMed  Google Scholar 

  18. Kumar AS, Ghule VD, Subrahmanyam S, Sahoo AK. Chem Eur J, 2013, 19: 509–518

    Article  CAS  PubMed  Google Scholar 

  19. Hawker CJ, Fokin VV, Finn MG, Sharpless KB. Aust J Chem, 2007, 60: 381–383

    Article  CAS  Google Scholar 

  20. Chu C, Liu R. Chem Soc Rev, 2011, 40: 2177–2188

    Article  CAS  PubMed  Google Scholar 

  21. Astruc D, Liang L, Rapakousiou A, Ruiz J. Acc Chem Res, 2012, 45: 630–640

    Article  CAS  PubMed  Google Scholar 

  22. Leophairatana P, Samanta S, De Silva CC, Koberstein JT. J Am Chem Soc, 2017, 139: 3756–3766

    Article  CAS  PubMed  Google Scholar 

  23. Huisgen R. Angew Chem Int Ed Engl, 1963, 2: 565–598

    Article  Google Scholar 

  24. Kolb HC, Finn MG, Sharpless KB. Angew Chem Int Ed, 2001, 40: 2004–2021

    Article  CAS  Google Scholar 

  25. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew Chem Int Ed, 2002, 41: 2596–2599

    Article  CAS  Google Scholar 

  26. Tornøe CW, Christensen C, Meldal M. J Org Chem, 2002, 67: 3057–3064

    Article  CAS  PubMed  Google Scholar 

  27. Fokin VV. In: Ding K, ai L-X, eds. Organic Chemistry-Breakthroughs and Perspectives. Weinheim: Wiley-VCH, 2012. 247–277

    Chapter  Google Scholar 

  28. Banert K. In: Bräse S, Banert K, Eds. Organic Azides: Syntheses and Applications. Chichester: Wiley, 2010

    Google Scholar 

  29. Wei F, Wang W, Ma Y, Tung CH, Xu Z. Chem Commun, 2016, 52: 14188–14199

    Article  CAS  Google Scholar 

  30. Kappe CO, Van der Eycken E. Chem Soc Rev, 2010, 39: 1280–1290

    Article  CAS  PubMed  Google Scholar 

  31. Johansson JR, Beke-Somfai T, Said Stålsmeden A, Kann N. Chem Rev, 2016, 116: 14726–14768

    Article  CAS  PubMed  Google Scholar 

  32. Wang Z, Li B, Zhang X, Fan X. J Org Chem, 2016, 81: 6357–6363

    Article  CAS  PubMed  Google Scholar 

  33. Wang Q, Shi X, Zhang X, Fan X. Org Biomol Chem, 2017, 15: 8529–8534

    Article  CAS  PubMed  Google Scholar 

  34. Kim WG, Kang ME, Lee JB, Jeon MH, Lee S, Lee J, Choi B, Cal PMSD, Kang S, Kee JM, Bernardes GJL, Rohde JU, Choe W, Hong SY. J Am Chem Soc, 2017, 139: 12121–12124

    Article  CAS  PubMed  Google Scholar 

  35. Zhu L, Zhang H, Wang C, Chen Z. Chin J Org Chem, 2018, 38: 1052–1064

    Article  CAS  Google Scholar 

  36. Chen Y, Liu Y, Petersen JL, Shi X. Chem Commun, 2008, 2: 3254–3256

    Article  CAS  Google Scholar 

  37. Kalisiak J, Sharpless KB, Fokin VV. Org Lett, 2008, 10: 3171–3174

    Article  CAS  PubMed  Google Scholar 

  38. Wang XJ, Sidhu K, Zhang L, Campbell S, Haddad N, Reeves DC, Krishnamurthy D, Senanayake CH. Org Lett, 2009, 11: 5490–5493

    Article  CAS  PubMed  Google Scholar 

  39. Wang X, Zhang L, Krishnamurthy D, Senanayake CH, Wipf P. Org Lett, 2010, 12: 4632–4635

    Article  CAS  PubMed  Google Scholar 

  40. Yan W, Wang Q, Chen Y, Petersen JL, Shi X. Org Lett, 2010, 12: 3308–3311

    Article  CAS  PubMed  Google Scholar 

  41. Liu Y, Yan W, Chen Y, Petersen JL, Shi X. Org Lett, 2008, 10: 5389–5392

    Article  CAS  PubMed  Google Scholar 

  42. Zhang Y, Ye X, Petersen JL, Li M, Shi X. J Org Chem, 2015, 80: 3664–3669

    Article  CAS  PubMed  Google Scholar 

  43. Wang X, Zhang L, Lee H, Haddad N, Krishnamurthy D, Senanayake CH. Org Lett, 2009, 11: 5026–5028

    Article  CAS  PubMed  Google Scholar 

  44. Ueda S, Su M, Buchwald SL. Angew Chem Int Ed, 2011, 50: 8944–8947

    Article  CAS  Google Scholar 

  45. Ueda S, Ali S, Fors BP, Buchwald SL. J Org Chem, 2012, 77: 2543–2547

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  46. Guru MM, Punniyamurthy T. J Org Chem, 2012, 77: 5063–5073

    Article  CAS  PubMed  Google Scholar 

  47. Stewart S, Harris R, Jamieson C. Synlett, 2014, 25: 2480–2484

    Article  CAS  Google Scholar 

  48. Wu L, Guo S, Wang X, Guo Z, Yao G, Lin Q, Wu M. Tetrahedron Lett, 2015, 56: 2145–2148

    Article  CAS  Google Scholar 

  49. Gavlik KD, Lesogorova SG, Sukhorukova ES, Subbotina JO, Slepukhin PA, Benassi E, Belskaya NP. Eur J Org Chem, 2016, 2016: 2700–2710

    Article  CAS  Google Scholar 

  50. Zhou J, He J, Wang B, Yang W, Ren H. J Am Chem Soc, 2011, 133: 6868–6870

    Article  CAS  PubMed  Google Scholar 

  51. Ryu T, Min J, Choi W, Jeon WH, Lee PH. Org Lett, 2014, 16: 2810–2813

    Article  CAS  PubMed  Google Scholar 

  52. Li J, Zhou H, Zhang J, Yang H, Jiang G. Chem Commun, 2016, 52: 9589–9592

    Article  CAS  Google Scholar 

  53. Kamijo S, Jin T, Huo Z, Yamamoto Y. J Org Chem, 2003, 69: 2386–2393

    Article  CAS  Google Scholar 

  54. Kalisiak J, Sharpless KB, Fokin VV. Org Lett, 2008, 10: 3171–3174

    Article  CAS  PubMed  Google Scholar 

  55. Peshkov VA, Pereshivko OP, Nechaev AA, Peshkov AA, Van der Eycken EV. Chem Soc Rev, 2018, 47: 3861–3898

    Article  CAS  PubMed  Google Scholar 

  56. Boyarskiy VP, Ryabukhin DS, Bokach NA, Vasilyev AV. Chem Rev, 2016, 116: 5894–5986

    Article  CAS  PubMed  Google Scholar 

  57. Yang L, Huang H. Chem Rev, 2015, 115: 3468–3517

    Article  CAS  PubMed  Google Scholar 

  58. Dorel R, Echavarren AM. Chem Rev, 2015, 115: 9028–9072

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  59. Asiri AM, Hashmi ASK. Chem Soc Rev, 2016, 45: 4471–4503

    Article  CAS  PubMed  Google Scholar 

  60. Zeng X. Chem Rev, 2013, 113: 6864–6900

    Article  CAS  PubMed  Google Scholar 

  61. Müller DS, Marek I. Chem Soc Rev, 2016, 45: 4552–4566

    Article  PubMed  PubMed Central  Google Scholar 

  62. Fang G, Bi X. Chem Soc Rev, 2015, 44: 8124–8173

    Article  CAS  PubMed  Google Scholar 

  63. Sekine K, Yamada T. Chem Soc Rev, 2016, 45: 4524–4532

    Article  CAS  PubMed  Google Scholar 

  64. Ning Y, Ji Q, Liao P, Anderson EA, Bi X. Angew Chem Int Ed, 2017, 56: 13805–13808

    Article  CAS  Google Scholar 

  65. Sadamitsu Y, Komatsuki K, Saito K, Yamada T. Org Lett, 2017, 19: 3191–3194

    Article  CAS  PubMed  Google Scholar 

  66. Wang H, Mi P, Zhao W, Kumar R, Bi X. Org Lett, 2017, 19: 5613–5616

    Article  CAS  PubMed  Google Scholar 

  67. Liu Z, Li Q, Liao P, Bi X. Chem Eur J, 2017, 23: 4756–4760

    Article  CAS  PubMed  Google Scholar 

  68. Barve IJ, Thikekar TU, Sun CM. Org Lett, 2017, 19: 2370–2373

    Article  CAS  PubMed  Google Scholar 

  69. Tang J, Sivaguru P, Ning Y, Zanoni G, Bi X. Org Lett, 2017, 19: 4026–4029

    Article  CAS  PubMed  Google Scholar 

  70. Liu JQ, Shen X, Wang Y, Wang XS, Bi X. Org Lett, 2018, 20: 6930–6933

    Article  CAS  PubMed  Google Scholar 

  71. Liu Z, Ji H, Gao W, Zhu G, Tong L, Lei F, Tang B. Chem Commun, 2017, 53: 6259–6262

    Article  CAS  Google Scholar 

  72. Xu T, Hu X. Angew Chem Int Ed, 2015, 54: 1307–1311

    Article  CAS  Google Scholar 

  73. Shen T, Wang T, Qin C, Jiao N. Angew Chem Int Ed, 2013, 52: 6677–6680

    Article  CAS  Google Scholar 

  74. Meier BW, Gomez JD, Zhou A, Thompson JA. Chem Res Toxicol, 2005, 18: 1575–1585

    Article  CAS  PubMed  Google Scholar 

  75. Lemercier JN, Meier BW, Gomez JD, Thompson JA. Chem Res Toxicol, 2004, 17: 1675–1683

    Article  CAS  PubMed  Google Scholar 

  76. Kupfer R, Dwyer-Nield LD, Malkinson AM, Thompson JA. Chem Res Toxicol, 2002, 15: 1106–1112

    Article  CAS  PubMed  Google Scholar 

  77. Zhou Q, Turnbull KD. J Org Chem, 2001, 66: 7072–7077

    Article  CAS  PubMed  Google Scholar 

  78. (a) CCDC 1849952 of 3a-N1 (b) CCDC 1881654 of 3f-N2 (c) CCDC 1898986 of 3x (d) CCDC 1881653 of 4h (e) CCDC 1898987 of 4n. All the supplementary crystallographic data for this paper are from Cambridge Crystallographic Data Centre http://www.ccdc.cam.ac.uk/

  79. Creary X, Anderson A, Brophy C, Crowell F, Funk Z. J Org Chem, 2012, 77: 8756–8761

    Article  CAS  PubMed  Google Scholar 

  80. Jin T, Kamijo S, Yamamoto Y. Eur J Org Chem, 2004, 2004: 3789–3791

    Article  CAS  Google Scholar 

  81. Vitérisi A, Orsini A, Weibel JM, Pale P. Tetrahedron Lett, 2006, 47: 2779–2781

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21535004, 91753111, 21605097, 21775092, 21390411), the Key Research and Development Program of Shandong Province (2018YFJH0502), the Natural Science Foundation of Shandong Province of China (ZR2016BQ01, ZR2018JL008) and the China Postdoctoral Science Foundation (2017M610442).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan, 250014, China

    Zhenhua Liu, Wenjing Hao, Wen Gao, Guangyu Zhu, Xiang Li, Lili Tong & Bo Tang

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  1. Zhenhua Liu
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  2. Wenjing Hao
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  3. Wen Gao
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  4. Guangyu Zhu
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  5. Xiang Li
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  6. Lili Tong
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  7. Bo Tang
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Correspondence to Wen Gao or Bo Tang.

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Liu, Z., Hao, W., Gao, W. et al. Silver-catalyzed three-component reaction: synthesis of N2-substituted 1,2,3-triazoles via direct benzylic amination. Sci. China Chem. 62, 1001–1006 (2019). https://doi.org/10.1007/s11426-019-9455-0

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